(9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Base Information

• Chemical Name: (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene
• CAS No.: 244769-38-8
• Molecular Formula: C₂₈H₂₈N₂O₇
• Molecular Weight: 504.54

Synonyms:(9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property of (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property:

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Technology Process of (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

There total 15 articles about (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(9S,12S)-17-Amino-12-benzyloxycarbonylamino-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3,5,7(19),14(18),15-hexaene-9-carboxylic acid methyl ester (244769-46-8) → (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (244769-38-8)

Guidance literature:

With copper(I) oxide; hypophosphorous acid; sodium nitrite; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/jo990432w

Reference yield:

3-(3-isopropoxy-4-methoxy-phenyl)-propionic acid → (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (244769-38-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine / tetrahydrofuran / 1 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.2: 83 percent / trisyl azide / tetrahydrofuran; toluene / 0.03 h / -78 °C

4.1: MeMgBr / diethyl ether / 0.03 h / 0 °C

4.2: 96 percent / diethyl ether / 0.17 h / 0 °C

5.1: 99 percent / hydrogen / Pd/C / methanol / 1 h

6.1: 90 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.33 h / 20 °C

7.1: BCl₃ / CH₂Cl₂ / -78 - 0 °C

7.2: 99 percent / Boc₂O; triethylamine / tetrahydrofuran / 2 h / 20 °C

8.1: potassium carbonate; molecular sieves 3A / dimethylsulfoxide / 2 h / 20 °C

9.1: trifluoroacetic acid / 0.33 h / 20 °C

9.2: 95 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C

10.1: 13.0 mg / SnCl₂*2H₂O / dimethylformamide / 2 h / 50 °C

11.1: 10.3 mg / H₃PO₂; Cu₂O; NaNO₂ / tetrahydrofuran; H₂O / 0 - 20 °C

With copper(I) oxide; n-butyllithium; 3 A molecular sieve; methylmagnesium bromide; hydrogen; hypophosphorous acid; boron trichloride; potassium hexamethylsilazane; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Acylation / 2.1: Metallation / 2.2: Substitution / 3.1: Metallation / 3.2: Substitution / 4.1: Substitution / 4.2: Substitution / 5.1: Hydrogenolysis / 6.1: coupling / 7.1: Hydrolysis / 7.2: Acylation / 8.1: Cyclization / 9.1: Hydrolysis / 9.2: Acylation / 10.1: Reduction / 11.1: Diazotization;

DOI:10.1021/jo990432w

Reference yield:

(2S)-methyl 2-azido-3-(3-isopropyloxy-4-methoxyphenyl)propionate (244769-34-4) → (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (244769-38-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / hydrogen / Pd/C / methanol / 1 h

2.1: 90 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.33 h / 20 °C

3.1: BCl₃ / CH₂Cl₂ / -78 - 0 °C

3.2: 99 percent / Boc₂O; triethylamine / tetrahydrofuran / 2 h / 20 °C

4.1: potassium carbonate; molecular sieves 3A / dimethylsulfoxide / 2 h / 20 °C

5.1: trifluoroacetic acid / 0.33 h / 20 °C

5.2: 95 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C

6.1: 13.0 mg / SnCl₂*2H₂O / dimethylformamide / 2 h / 50 °C

7.1: 10.3 mg / H₃PO₂; Cu₂O; NaNO₂ / tetrahydrofuran; H₂O / 0 - 20 °C

With copper(I) oxide; 3 A molecular sieve; hydrogen; hypophosphorous acid; boron trichloride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Hydrogenolysis / 2.1: coupling / 3.1: Hydrolysis / 3.2: Acylation / 4.1: Cyclization / 5.1: Hydrolysis / 5.2: Acylation / 6.1: Reduction / 7.1: Diazotization;

DOI:10.1021/jo990432w

upstream raw materials:

(9S,12S)-17-Amino-12-benzyloxycarbonylamino-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester

(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-hydroxy-9-methoxycarbonyl-16-nitro-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

methyl N-[N-(tert-butyloxycarbonyl)-L-(3,4-dihydroxyphenylalanyl)]-L-4-fluoro-3-nitrophenylalanine

L-methyl 3-isopropyloxy-4-methoxyphenylalaninate

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